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By nature, we humans shrink from anything that seems possibly painful or overtly difficult. We bring this natural tendency to our practice of any skill. Once we grow adept at some aspect of this skill, generally one that comes more easily to us, we prefer to practice this element over and over. Our skill becomes lopsided as we avoid our weaknesses. Knowing that in our practice we can let down our guard, since we are not being watched or under pressure to perform, we bring to this a kind of dispersed attention. We tend to also be quite conventional in our practice routines. We generally follow what others have done, performing the accepted exercises for these skills.

This is the path of amateurs. To attain mastery, you must adopt what we shall call Resistance Practice. The principle is simple—you go in the opposite direction of all of your natural tendencies when it comes to practice. First, you resist the temptation to be nice to yourself. You become your own worst critic; you see your work as if through the eyes of others. You recognize your weaknesses, precisely the elements you are not good at. Those are the aspects you give precedence to in your practice. You find a kind of perverse pleasure in moving past the pain this might bring. Second, you resist the lure of easing up on your focus. You train yourself to concentrate in practice with double the intensity, as if it were the real thing times two. In devising your own routines, you become as creative as possible. You invent exercises that work upon your weaknesses. You give yourself arbitrary deadlines to meet certain standards, constantly pushing yourself past perceived limits. In this way you develop your own standards for excellence, generally higher than those of others.

In the end, your five hours of intense, focused work are the equivalent of ten for most people. Soon enough you will see the results of such practice, and others will marvel at the apparent ease in which you accomplish your deeds.

Apprentice yourself in failure

One day in 1885, the twenty-three-year old Henry Ford got his first look at the gas-powered engine, and it was instant love. Ford had apprenticed as a machinist and had worked on every conceivable device, but nothing could compare to his fascination with this new type of engine, one that created its own power. He envisioned a whole new kind of horseless carriage that would revolutionize transportation. He made it his Life’s Task to be the pioneer in developing such an automobile.

Working the night shift at the Edison Illuminating Company as an engineer, during the day he would tinker with the new internal-combustion engine he was developing. He built a workshop in a shed behind his home and started constructing the engine from pieces of scrap metal he salvaged from anywhere he could find them. By 1896, working with friends who helped him build a carriage, he completed his first prototype, which he called the Quadricycle, and debuted it on the streets of Detroit.

At the time there were many others working on automobiles with gas-powered engines. It was a ruthlessly competitive environment in which new companies died by the day. Ford’s Quadricycle looked nice and ran well, but it was too small and incomplete for large-scale production. And so he began work on a second automobile, thinking ahead to the production end of the process. A year later he completed it, and it was a marvel of design. Everything was geared toward simplicity and compactness. It was easy to drive and maintain. All that he needed was financial backing and sufficient capital to mass-produce it.

To manufacture automobiles in the late 1890s was a daunting venture. It required a tremendous amount of capital and a complex business structure, considering all of the parts that went into production. Ford quickly found the perfect backer: William H. Murphy, one of the most prominent businessmen in Detroit. The new company was dubbed the Detroit Automobile Company, and all who were involved had high hopes. But problems soon arose. The car Ford had designed as a prototype needed to be reworked—the parts came from different places; some of them were deficient and far too heavy for his liking. He kept trying to refine the design to come closer to his ideal. But it was taking far too long, and Murphy and the stockholders were getting restless. In 1901, a year and a half after it had started operation, the board of directors dissolved the company. They had lost faith in Henry Ford.

In analyzing this failure, Ford came to the conclusion that he had been trying to make his automobile serve too many consumer needs. He would try a second time, starting out with a lightweight and smaller vehicle. He convinced Murphy to give him another chance, something rare in the fledgling automobile business. Still believing in Ford’s genius, he agreed, and together they formed the Henry Ford Company. Right from the start, however, Ford felt the pressure from Murphy to get the automobile ready for production so as to avoid the problems he’d had with the first company. Ford resented the interference from people who knew nothing about design or the high standards he was trying to establish for the industry.

Murphy and his men brought in an outsider to supervise the process. This was the breaking point—less than a year after its establishment, Ford left the company. The break with Murphy this time was final. In the car business, everyone wrote Henry Ford off. He had blown his two chances and nobody was ever given a third, not with the amount of money at stake. But to friends and family, Ford himself seemed blithely unconcerned. He told everyone that these were all invaluable lessons to him—he had paid attention to every glitch along the way, and like a watch or an engine, he had taken apart these failures in his mind and had identified the root cause: no one was giving him enough time to work out the bugs. The people with money were meddling in mechanical and design affairs. They were injecting their mediocre ideas into the process and polluting it. He resented the idea that having money gave them certain rights, when all that mattered was a perfect design.

The answer was to find a way to maintain complete independence from the financiers. This was not the usual way of doing business in America, which was becoming increasingly bureaucratic. He would have to invent his own form of organization, his own business model, one that suited his temperament and needs—including an efficient team he could trust, and the right to the final word on every decision.

Considering his reputation, it would be almost impossible to find backing, but several months into the search he found an ideal partner—Alexander Malcomson, an émigré from Scotland who had made his fortune in the coal business. Like Ford, he had an unconventional streak and was a risk taker. He agreed to finance this latest venture and to not meddle in the manufacturing process. Ford worked at creating a new kind of assembly plant that would give him more control over the car he wanted to design, now known as the Model A. The Model A would be the lightest car ever made, simple and durable. It was the culmination of all of his tinkering and designing. It would be assembled along a line that would ensure speed of production.

With the assembly plant ready, Ford worked hard at getting the team of workers to churn out fifteen cars a day—a rather high number back then. He oversaw every aspect of the production—it was his car from the inside out. He even worked on the assembly line, endearing himself to the workers. Orders started pouring in for the well made yet inexpensive Model A, and by 1904 the Ford Motor Company had to expand its operations. Soon it would be one of the few survivors from the early era of the automobile business, and a giant in the making.

Henry Ford had one of those minds that was naturally attuned to the mechanical. He had the power of most great inventors—the ability to visualize the parts and how they functioned together. If he had to describe how something worked, Ford would inevitably take a napkin and sketch out a diagram rather than use words. With this type of intelligence, his apprenticeships on machines were easy and fast. But when it came to mass-producing his inventions, he had to confront the fact that he did not have the requisite knowledge. He needed an additional apprenticeship in becoming a businessman and entrepreneur. Fortunately, working on machines had developed in him a kind of practical intelligence, patience, and way of solving problems that could be applied to anything.

When a machine malfunctions you do not take it personally or grow despondent. It is in fact a blessing in disguise. Such malfunctions generally show you inherent flaws and means of improvement. You simply keep tinkering until you get it right. The same should apply to an entrepreneurial venture. Mistakes and failures are precisely your means of education. They tell you about your own inadequacies. It is hard to find out such things from people, as they are often political with their praise and criticisms. Your failures also permit you to see the flaws of your ideas, which are only revealed in the execution of them. You learn what your audience really wants, the discrepancy between your ideas and how they affect the public. Pay close attention to the structure of your group—how your team is organized, the degree of independence you have from the source of capital. These are design elements as well, and such management issues are often hidden sources of problems.

Think of it this way: There are two kinds of failure. The first comes from never trying out your ideas because you are afraid, or because you are waiting for the perfect time. This kind of failure you can never learn from, and such timidity will destroy you. The second kind comes from a bold and venturesome spirit. If you fail in this way, the hit that you take to your reputation is greatly outweighed by what you learn. Repeated failure will toughen your spirit and show you with absolute clarity how things must be done. In fact, it is a curse to have everything go right on your first attempt. You will fail to question the element of luck, making you think that you have the golden touch. When you do inevitably fail, it will confuse and demoralize you past the point of learning. In any case, to apprentice as an entrepreneur you must act on your ideas as early as possible, exposing them to the public, a part of you even hoping that you’ll fail. You have everything to gain.

Combine the “how” and the “what”

At a very early age, Santiago Calatrava (b. 1951) developed a love for drawing. He carried his pencils wherever he went. A certain paradox in drawing began to obsess him. In Valencia, Spain, where he grew up, the harsh Mediterranean sunlight would place in sharp relief the things he liked to draw—rocks, trees, buildings, people. Their outlines would slowly soften as the day progressed. Nothing he drew was ever really static; everything is in a state of change and motion—that is the essence of life. How could he capture this movement on paper, in an image that was perfectly still?

He took classes and learned techniques for creating the various illusions of something caught in the moment of movement, but it was never quite enough. As part of this impossible quest he taught himself aspects of mathematics, such as descriptive geometry, that could help him understand how to represent his objects in two dimensions. His skill improved and his interest in the subject deepened. It seemed he was destined for a career as an artist, and so in 1969 he enrolled in art school in Valencia.

A few months into his studies, he had a seemingly minor experience that would change the course of his life: browsing for supplies in a stationery store, his eye was drawn to a beautifully designed booklet describing the work of the great architect Le Corbusier. Somehow this architect had managed to create completely distinctive shapes. He turned even something as simple as a stairway into a dynamic piece of sculpture. The buildings he designed seemed to defy gravity, creating a feeling of movement in their still forms. Studying this booklet, Calatrava now developed a new obsession—to learn the secret of how such buildings came about. As soon as he could, he transferred to the one architecture school in Valencia.

Graduating from the school in 1973, Calatrava had gained a solid education in the subject. He had learned all of the most important design rules and principles. He was more than capable of taking his place in some architecture firm and working his way up. But he felt something elemental was missing in his knowledge. In looking at all of the great works of architecture that he most admired—the Pantheon in Rome, the buildings of Gaudí in Barcelona, the bridges designed by Robert Maillart in Switzerland—he had no solid idea about their actual construction. He knew more than enough about their form, their aesthetics, and how they functioned as public buildings, but he knew nothing about how they stood up, how the pieces fit together, how the buildings of Le Corbusier managed to create that impression of movement and dynamism.

It was like knowing how to draw a beautiful bird but not understanding how it could fly. As with drawing, he wanted to go beyond the surface, the design element, and touch upon the reality. He felt that the world was changing; something was in the air. With advances in technology and new materials, revolutionary possibilities had emerged for a new kind of architecture, but to truly exploit that he would have to learn something about engineering. Thinking in this direction, Calatrava made a fateful decision—he would virtually start over and enroll at the Federal Institute of Technology in Zurich, Switzerland, to gain a degree in civil engineering. It would be an arduous process, but he would train himself to think and draw like an engineer. Knowing how buildings were constructed would liberate him and give him ideas about how to slowly expand the boundaries of what could be made.

In the first few years he grounded himself in the rigors of engineering—all of the mathematics and physics required for the field. But as he progressed, he found himself returning to that paradox that he had been obsessed with in childhood—how to express movement and change. In architecture, the golden rule was that buildings had to be stable and stationary. Calatrava felt the desire to break up this rigid convention. For his PhD dissertation, he decided to explore the possibilities of bringing actual movement into architecture. Inspired by NASA and its designs for space travel, as well as the folding bird wings designed by Leonardo da Vinci, Calatrava chose as his topic the foldability of structures—how through advanced engineering structures could move and transform themselves.

Completing his dissertation in 1981, he finally entered the work world—after fourteen years of a university apprenticeship in art, architecture, and engineering. In the coming years he would experiment in designing new kinds of collapsible doors, windows, and roofs that would move and open up in new ways, altering the shape of the building. He designed a drawbridge in Buenos Aires that moved outward instead of up. In 1996 he took all of this a step further with his design and construction of an extension to the Milwaukee Art Museum. It consisted of a long glass-and-steel reception hall with an eighty-foot ceiling, all shaded by an enormous moveable sunscreen on the roof. The screen had two ribbed panels that opened and closed like the wings of a giant seagull, putting the entire edifice into motion, and giving the sense of a building that could take flight.

We humans live in two worlds. First, there is the outer world of appearances—all of the forms of things that captivate our eye. But hidden from our view is another world—how these things actually function, their anatomy or composition, the parts working together and forming the whole. This second world is not so immediately captivating. It is harder to understand. It is not something visible to the eye, but only to the mind that glimpses the reality. But this “how” of things is just as poetic once we understand it—it contains the secret of life, of how things move and change.

This division between the “how” and the “what” can be applied to almost everything around us—we see the machine, not how it works; we see a group of people producing something as a business, not how the group is structured or how the products are manufactured and distributed. (In a similar fashion, we tend to be mesmerized by people’s appearances, not the psychology behind what they do or say.) As Calatrava discovered, in overcoming this division, in combining the “how” and the “what” of architecture, he gained a much deeper, or rather more rounded knowledge of the field. He grasped a larger portion of the reality that goes into making buildings. This allowed him to create something infinitely more poetic, to stretch the boundaries, to break the conventions of architecture itself.

Understand: we live in the world of a sad separation that began some five hundred years ago when art and science split apart. Scientists and technicians live in their own world, focusing mostly on the “how” of things. Others live in the world of appearances, using these things but not really understanding how they function. Just before this split occurred, it was the ideal of the Renaissance to combine these two forms of knowledge. This is why the work of Leonardo da Vinci continues to fascinate us, and why the Renaissance remains an ideal. This more rounded knowledge is in fact the way of the future, especially now that so much more information is available to all of us. As Calatrava intuited, this should be a part of our apprenticeship. We must make ourselves study as deeply as possible the technology we use, the functioning of the group we work in, the economics of our field, its lifeblood. We must constantly ask the questions—how do things work, how do decisions get made, how does the group interact? Rounding our knowledge in this way will give us a deeper feel for reality and the heightened power to alter it.

Advance through trial and error

Growing up in a suburb of Pittsburgh, Pennsylvania, in the early 1970s, Paul Graham (b. 1964) became fascinated with the depiction of computers in television and film. They were like electronic brains with limitless powers. In the near future, or so it seemed, you would be able to talk to your computer, and it would do everything you wanted.

In junior high school he had been admitted into a program for gifted students that provided them with the chance to work on a creative project of their choosing. Graham decided to focus his project on the school’s computer, an IBM mainframe that was used for printing out grade reports and class schedules. This was the first time he had gotten his hands on a computer, and although it was primitive and had to be programmed with punch cards, it seemed like something magical—a portal to the future.

Over the next few years, he taught himself how to program by consulting the few books then written on the subject, but mostly he learned by trial and error. Like painting on a canvas, he could see the results immediately of what he had done—and if the programming worked, it had a certain aesthetic rightness to it. The process of learning through trial and error was immensely satisfying. He could discover things on his own, without having to follow a rigid path set up by others. (This is the essence of being a “hacker.”) And the better he got at programming, the more he could make it do.

Deciding to pursue his studies further, he chose to attend Cornell University, which at the time had one of the best computer science departments in the country. Here he finally received instruction in the basic principles of programming, cleaning up many of the bad hacking habits he had developed on his own. He became intrigued by the recently developed field of artificial intelligence—the key to designing the kinds of computers he had dreamed about as a child. To be on the frontier of this new field, he applied and was accepted to the graduate school in computer science at Harvard University.

At Harvard Graham finally had to confront something about himself—he was not cut out for academia. He hated writing research papers. The university way of programming took all the fun and excitement out of it—the process of discovering through trial and error. He was a hacker at heart, one who liked to figure things out for himself. He found a fellow hacker at Harvard, Robert Morris, and together they began to explore the intricacies of the programming language Lisp. It seemed like the most potentially powerful and fluid language of them all. Understanding Lisp made you understand something essential about programming itself. It was a language suited for high-level hackers, a language specifically made for investigation and discovery.

Disillusioned with the computer science department at Harvard, Graham decided to design his own graduate school program: he would take a wide range of classes and discover what interested him the most. To his surprise, he found himself attracted to art—to painting, and to the subject of art history itself. What this meant to him was that he should follow this interest and see where it would lead. After completing his PhD at Harvard in computer science, he enrolled in the Rhode Island School of Design, then attended a painting program at the Accademia in Florence, Italy. He returned to the States broke but determined to try his hand at painting. He would pay for his lifestyle with intermittent consulting work in programming.

As the years went by, he would occasionally reflect on the course of his life. Artists in the Renaissance would go through clear-cut apprenticeships, but what could he say about his own apprenticeship? There seemed to be no real design or direction to his life. It was like the “cheesy hacks” he did in high school, patching things together, figuring things out through constant trial and error, finding out what worked by doing it. Shaping his life in this haphazard way, he learned what to avoid—academia; working for large companies; any political environment. He liked the process of making things. What really mattered to him in the end was having possibilities—being able to go in this or that direction, depending on what life presented to him. If over the years he had undergone an apprenticeship, it was almost by default.

One afternoon in 1995, he heard on the radio a story about Netscape—the company itself was touting its future and discussing how someday most businesses would be selling their products on the Internet itself, with Netscape leading the way. With his bank account getting desperately low again, yet dreading the idea of returning to another consulting job, he recruited his old hacker friend Robert Morris to help him create software for running an online business. Graham’s idea was to design a program that would run directly on the web server instead of having to be downloaded. No one had thought of this before. They would write the program in Lisp, taking advantage of the speed with which they could make changes to it. They called their business Viaweb, and it would be the first of its kind, the pioneer of online commerce. Just three years later they sold it to Yahoo! for $45 million.

In the years to come Graham would continue on the path set in his twenties, moving to where his interests and skills converged, to wherever he could see possibilities. In 2005 he gave a talk at Harvard about his experiences with Viaweb. The students, excited by his advice, pleaded with him to start up some kind of consulting firm. Intrigued by the idea, he created Y Combinator, an apprenticeship system for young entrepreneurs in technology, with his company taking a stake in each successful startup. Over the years he would refine the system, learning as he went along. In the end, Y Combinator represented his ultimate hack—something he came upon by accident and improved through his own process of trial and error. The company is now valued at close to $500 million.

Each age tends to create a model of apprenticeship that is suited to the system of production that prevails at the time. In the Middle Ages, during the birth of modern capitalism and the need for quality control, the first apprenticeship system appeared, with its rigidly defined terms. With the advent of the Industrial Revolution, this model of apprenticeship became largely outmoded, but the idea behind it lived on in the form of self-apprenticeship—developing yourself from within a particular field, as Darwin did in biology. This suited the growing individualistic spirit of the time. We are now in the computer age, with computers dominating nearly all aspects of commercial life. Although there are many ways in which this could influence the concept of apprenticeship, it is the hacker approach to programming that may offer the most promising model for this new age.

The model goes like this: You want to learn as many skills as possible, following the direction that circumstances lead you to, but only if they are related to your deepest interests. Like a hacker, you value the process of self-discovery and making things that are of the highest quality. You avoid the trap of following one set career path. You are not sure where this will all lead, but you are taking full advantage of the openness of information, all of the knowledge about skills now at our disposal. You see what kind of work suits you and what you want to avoid at all cost. You move by trial and error. This is how you pass your twenties. You are the programmer of this wide-ranging apprenticeship, within the loose constraints of your personal interests.

You are not wandering about because you are afraid of commitment, but because you are expanding your skill base and your possibilities. At a certain point, when you are ready to settle on something, ideas and opportunities will inevitably present themselves to you. When that happens, all of the skills you have accumulated will prove invaluable. You will be the Master at combining them in ways that are unique and suited to your individuality. You may settle on this one place or idea for several years, accumulating in the process even more skills, then move in a slightly different direction when the time is appropriate. In this new age, those who follow a rigid, singular path in their youth often find themselves in a career dead end in their forties, or overwhelmed with boredom. The wide-ranging apprenticeship of your twenties will yield the opposite—expanding possibilities as you get older.

REVERSAL

It might be imagined that certain people in history—the naturally gifted, the geniuses—have either somehow bypassed the Apprenticeship Phase or have greatly shortened it because of their inherent brilliance. To support such an argument, people will bring up the classic examples of Mozart and Einstein, who seemed to have emerged as creative geniuses out of nowhere.

With the case of Mozart, however, it is generally agreed among classical music critics that he did not write an original and substantial piece of music until well after ten years of composing. In fact, a study of some seventy great classical composers determined that with only three exceptions, all of the composers had needed at least ten years to produce their first great work, and the exceptions had somehow managed to create theirs in nine years.

Einstein began his serious thought experiments at the age of sixteen. Ten years later he came up with his first revolutionary theory of relativity. It is impossible to quantify the time he spent honing his theoretical skills in those ten years, but is not hard to imagine him working three hours a day on this particular problem, which would yield more than 10,000 hours after a decade. What in fact separates Mozart and Einstein from others is the extreme youth with which they began their apprenticeships and the intensity with which they practiced, stemming from their total immersion in the subject. It is often the case that in our younger years we learn faster, absorb more deeply, and yet retain a kind of creative verve that tends to fade as we get older.

There are no shortcuts or ways to bypass the Apprenticeship Phase. It is the nature of the human brain to require such lengthy exposure to a field, which allows for complex skills to become deeply embedded and frees the mind up for real creative activity. The very desire to find shortcuts makes you eminently unsuited for any kind of mastery. There is no possible reversal to this process.

It’s like chopping down a huge tree of immense girth. You won’t accomplish it with one swing of your axe. If you keep chopping away at it, though, and do not let up, eventually, whether it wants to or not, it will suddenly topple down. When that time comes, you could round up everyone you could find and pay them to hold the tree up, but they wouldn’t be able to do it. It would still come crashing to the ground…. But if the woodcutter stopped after one or two strokes of his axe to ask the third son of Mr. Chang, “Why doesn’t this tree fall?” And after three or four more strokes stopped again to ask the fourth son of Mr. Li, “Why doesn’t this tree fall?” he would never succeed in felling the tree. It is no different for someone who is practicing the Way .